A startup isn't meant to make you happy

It doesn't mean you should stop being a founder, but it does mean you should reflect on your expectations

Running a startup is not meant to make you happy. Is it ok if I use myself as an example here?

First, let’s talk about how I’ve been living my life.

I moved to London in 2006, keen to “make it” but unsure about what it meant. I remember wandering around Selfridges as a student and thinking how cool it would be to make enough money to shop there day-to-day and maybe even live around the corner in Mayfair.

I built a cool startup. I was looking up to successful founders and was quite persuaded that if only my startup would sell for lots of money, then I’d be happy. I had a magic net worth number in my mind that was supposed to be the answer.

Clearly, that required a lot of work, which I did. London is expensive, but I’ll make more money if I work harder, right?

Even before I founded the startup, I got alopecia areata. ‘Lifestyle,’ said my GP. ‘Change your lifestyle.’

I didn’t listen, so a few years later, with a bit of founder stress on top, I was hit with a bigger stick: depression. And that was painful enough that I took a very, very deep breath and started thinking about how I’ve been living my life and what it means to be happy and content. I realised quite clearly that the trajectory I was on would literally kill me one day.

Let’s segue to a more positive topic: happiness.

Ever since that depressive episode in 2016, I’ve been gradually changing my life towards being happy. The more I learn about what it takes to be happy, the more I feel the tension between a focus on well-being and a focus on being successful in a conventional way.

So, what makes us happy?

People have been trying to figure out how to be happy since time immemorial, and they’ve learned a few things about what works and what doesn’t.

In short, here’s what works:

• accepting reality as it is instead of bending it to our will

• being virtuous: grateful, kind, compassionate, patient, etc.

• simple lifestyle and few needs

• seeing and experiencing yourself as part of nature and society

Here is what doesn’t:

• forcing the world to be the way you want it to be

• being greedy and manipulating others

• extravagant lifestyle

• seeing yourself as a hero, separate from the rest of the world

And here’s the problem. This last list is not far from how we’re conditioned to live our lives, especially as entrepreneurs. Let me give you a more upbeat version of the same list, but now from a PR team that was raised on Ayn Rand’s books:

Transform the world by embodying visionary leadership, strategically maximizing resources, and living a life that inspires, proving that individual determination can indeed shape the future.

Let’s get back to using me as an example. Can I tell you how I live my life? Here are the choices my fiancée and I made in the last few years:

• Live in a small coastal town, not in a big city

• Work remotely and flexibly doing what we love helping others (I’m a coach, she’s a yoga teacher)

• Meditate consistently

• Spend a lot of time with each other and in nature

• No back to back meetings (usually), enough sleep, slow mornings

• A simple flat without a mortgage over a house with one

• Not trying to build a VC-backed startup or make loads of money

• A pretty simple lifestyle.

Result? I’m infinitely happier and more satisfied with my life compared to when I had that depressive episode.

I’m far from being the only one asking questions.

Kirsten Powers

recently wrote:

I realized there are other places in the world (not just Italy) where life isn't about conspicuous consumption and "crushing" and "killing" your life goals, where people aren't drowning in debt just to pay for basic life necessities. There are places where people have free time and where that free time is used to do things they love — not to start a side hustle.

I started to have a dawning awareness that we don't have to live this way.

And this brings me to an interesting question. What do I say to my founder clients who are waking up at 3 am worried about their startup problems but who don’t want to live like this?

Should we stop running startups?

I know what it’s like to wake up at 3 am, I’ve been there. Does it mean that the answer is to stop running companies or try to do ambitious things?

I don’t believe so. The key to happiness is inside, in our attitudes, beliefs, worldviews, and in the state of our mind. There are plenty of happy people running startups and plenty of miserable ones who don’t. Some of my clients are pretty happy, yet they are running fast-paced startups.

Instead, the answer is more complex.

First, external circumstances matter. If your life is so complex that you have to have 12 meetings every day just to keep up, it will take its toll on your well-being. If you make this choice deliberately, that’s fair, but understand that if you try to push your mind and body faster than what they are meant to do, there will be a price to pay, for you and your families.

As I argued two weeks ago, it’s a valid choice as long as it’s time-limited and you understand the consequences. Consider it an occupational hazard, as if you were working with radioactive materials: fine if it’s for a while, deadly if you do it for a long time.

Second, the state of your mind matters greatly. The more I meditate, the more I realise how important mind training is. Our default state is blissful. If we sit quietly for long enough to avoid being disturbed by our mind, we inevitably get in touch with a deep source of unconditional calm and happiness. That’s one of the main lessons people learn on their first or second meditation retreat.

The point here isn’t to sit quietly and in bliss, of course. The point is to train your mind so that it’s not being continuously disturbed by its own thoughts, waking you up at 3 am. The point is to live your life without unnecessary worry, anxiety or rumination. If there’s no immediate physical threat to you, your mind can and should be calm and quiet, but it takes a lot of training and suitable life conditions.

Third, we absolutely must drop the belief that our happiness is conditional on anything or anyone external, on things changing or staying the same. This is a recipe for being unhappy. Any moment you feel dissatisfied, check: what is it that you want to be different? There will always be something you want to be different. The trouble is that the world will never be fully in line with your expectations, unless you don’t have any whatsoever.

The Great Way is not difficult for those who have no preferences. […] Make the smallest distinction, however, and heaven and earth are set infinitely apart.

Third Chinese Partiarch of Zen

Fourth, virtue matters more than having a calm mind. A kind, generous, compassionate, patient, honest person will be happier than a meditator who isn’t.

Fifth, life is complex and mysterious, and everyone’s situation is unique. There isn’t one size fits all answer. I, for one, was able to make the choices outlined above because I built a startup, which gave me experience, money and connections to make the life choices I made.

So when founders ask me how to live more sustainably and not to wake up at 3 am in the morning, I don’t tell them what to do. But I do help them see what’s going on and make sure their choices are deliberate.

The point is to live an examined and responsible life. What exactly it looks like for you — it’s your choice.

Happiness and well-being are a bold choice

There is a bigger context at play. Our entire society is pushing and conditioning us to live in a way that is just fundamentally not satisfying. I know a fair few wealthy and successful entrepreneurs. Are they happier than others? Sometimes, but if that’s the case, it’s not because of the money, but because of the inner work they’ve done.

Making a bold choice to put your well-being first (and that of your kids, by the way, because they’re influenced by you) can threaten our friendships, career prospects, social status and even a sense of self — quite rightly, because we’d be uprooting a sense of self built on the idea that we can only be happy by bending the world to our will.

It does take courage to choose to live differently from your friends and maybe even family. Yet, what’s the alternative?

Your life is precious and you don’t get it very often.

If you are lucky enough to have your basic needs covered — food, shelter, safety, companionship — you have the foundation to make choices about how you want to live your life.

If you sense that how we’re implicitly expected to live our lives isn’t compatible with what makes you happy, deep down, you’re not crazy.

The good news is that you can do something about it. What is your idea of a life well-lived?